DE3230768A1 - Azo-pigmentfarbstoffe - Google Patents
Azo-pigmentfarbstoffeInfo
- Publication number
- DE3230768A1 DE3230768A1 DE19823230768 DE3230768A DE3230768A1 DE 3230768 A1 DE3230768 A1 DE 3230768A1 DE 19823230768 DE19823230768 DE 19823230768 DE 3230768 A DE3230768 A DE 3230768A DE 3230768 A1 DE3230768 A1 DE 3230768A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- hydrogen
- alkyl
- parts
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 21
- 239000000975 dye Substances 0.000 title claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000004922 lacquer Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 229920000297 Rayon Polymers 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 230000008878 coupling Effects 0.000 abstract description 5
- 238000010168 coupling process Methods 0.000 abstract description 5
- 238000005859 coupling reaction Methods 0.000 abstract description 5
- -1 hydroxyl- Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- GLLRIXZGBQOFLM-UHFFFAOYSA-N Xanthorin Natural products C1=C(C)C=C2C(=O)C3=C(O)C(OC)=CC(O)=C3C(=O)C2=C1O GLLRIXZGBQOFLM-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823230768 DE3230768A1 (de) | 1981-08-28 | 1982-08-19 | Azo-pigmentfarbstoffe |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3134126 | 1981-08-28 | ||
| DE19823230768 DE3230768A1 (de) | 1981-08-28 | 1982-08-19 | Azo-pigmentfarbstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3230768A1 true DE3230768A1 (de) | 1983-03-10 |
| DE3230768C2 DE3230768C2 (enrdf_load_html_response) | 1990-02-22 |
Family
ID=25795610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823230768 Granted DE3230768A1 (de) | 1981-08-28 | 1982-08-19 | Azo-pigmentfarbstoffe |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3230768A1 (enrdf_load_html_response) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2066986A (en) * | 1933-03-01 | 1937-01-05 | Gen Aniline Works Inc | Water-insoluble azodyestuffs |
| US2209749A (en) * | 1937-05-22 | 1940-07-30 | Gen Aniline & Film Corp | Water-insoluble azo dyestuffs |
-
1982
- 1982-08-19 DE DE19823230768 patent/DE3230768A1/de active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2066986A (en) * | 1933-03-01 | 1937-01-05 | Gen Aniline Works Inc | Water-insoluble azodyestuffs |
| US2209749A (en) * | 1937-05-22 | 1940-07-30 | Gen Aniline & Film Corp | Water-insoluble azo dyestuffs |
Non-Patent Citations (2)
| Title |
|---|
| JP 52-115856 in CPI-Profile Booklet, 1978, 80268 Y/45 * |
| RATH, H.: Lehrbuch der Textilchemie, 3. Aufl., 1972, S.424 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3230768C2 (enrdf_load_html_response) | 1990-02-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0214445B1 (de) | Heterocyclische Azofarbstoffe | |
| DE4039590A1 (de) | Verfahren zur herstellung eines pigmentfarbstoffs mit verbesserten eigenschaften | |
| DE60102705T2 (de) | Hitzestabile monoazo magentapigmentzusammensetzungen | |
| DE2401597C2 (de) | Azoarylamide enthaltende Pigmentzusammensetzungen, ihre Herstellung und Verwendung | |
| CH653048A5 (de) | Azo-pigmentfarbstoffe. | |
| CH663216A5 (de) | Azo-pigmentfarbstoff-gemische. | |
| DE1219146B (de) | Verfahren zur Herstellung von wasserloeslichen Monoazofarbstoffen | |
| DE2800765C2 (de) | Neue Monoazopigmente, Verfahren zu deren Herstellung und deren Verwendung | |
| EP0162806B1 (de) | Monoazoverbindungen enthaltend mindestens eine Carbonamidgruppe | |
| DE3230768A1 (de) | Azo-pigmentfarbstoffe | |
| DE3501199A1 (de) | Azo-pigmentfarbstoffe | |
| DE2758407C2 (enrdf_load_html_response) | ||
| DE2130040C3 (de) | Wasserunlösliche Monoazoverbindüngen, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| CH676469A5 (enrdf_load_html_response) | ||
| DE1544345A1 (de) | Verfahren zur Herstellung neuer Benzthiazolylmonoazofarbstoffe | |
| DE2300940A1 (de) | Azopigmente | |
| DE2424538A1 (de) | Azofarbstoffe mit einem phthalazonrest | |
| DE2247009B2 (de) | Iminoisoindolinonfarbstoffe und Verwendung zum Pigmentieren von hochmolekularem organischem Material | |
| DE1069313C (enrdf_load_html_response) | ||
| AT207017B (de) | Verfahren zur Herstellung von neuen Pigmentfarbstoffen | |
| DE1644244C (de) | Monoazopigmentfarbstoff, Verfahren zu dessen Herstellung und dessen Verwendung | |
| DE2201242C3 (de) | Monoazopigmente, Verfahren zu deren Herstellung und ihre Verwendung | |
| DE2803992A1 (de) | Wasserunloesliche monoazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung | |
| DE3712946A1 (de) | Monoazopigmente | |
| DE2224010A1 (de) | Azopigmentfarbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CLARIANT FINANCE (BVI) LTD., TORTOLA, VG |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: SPOTT WEINMILLER & PARTNER, 80336 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |